Laboratoire de Glycochimie, des Antimicrobiens
et des Agroressources UMR 7378 CNRS


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Actualités et Publications

CHAPTER 4 Carbon Nanostructures and Polysaccharides for Biomedical Materials,

González-Domínguez, J. M.; Álvarez-Sánchez, M. Á.; Hadad, C.; Benito, A. M.; Maser, W. K.

Carbon Nanostructures for Biomedical Applications 2021, 98-152.

Even though many members from the broad family of carbon nanostructures have been known to us for decades, and despite their promising potential in biology and medicine, there is still a long way ahead to reach the goal of using them in real applications. The cause of such a gap still lies in the persistent drawbacks of insolubility, processability difficulties, poor consistency of macroscopic assemblies and surface inertness of carbon nanostructures. However, solely their direct chemical derivatization might not solve the problem right away. New processing elements need to come into play, but this also twists the whole picture, as the toxicity and performance profiles become more complex. We herein analyse the potential of natural polysaccharides (with a particular focus on cellulose) towards hybrid materials and structures for biomedical purposes. The role that these biopolymers acquire when interfacing with carbon nanostructures goes far beyond a mere dispersing effect, but instead creates unprecedented synergies leading to hydrogels, aerogels, films or fibres with high biocompatibility and bioactivity. In this chapter, the history of carbon nanostructures and natural polysaccharides in the field of biomedical applications will be respectively reviewed, to subsequently go into detail of specific hybrids made with the most relevant biopolymers (namely cellulose, chitin, chitosan and alginate) with extraordinary prospects in biomedicine.

First Steps to Rationalize Host–Guest Interaction between α-, β-, and γ-Cyclodextrin and Divalent First-Row Transition and Post-transition Metals (Subgroups VIIB, VIIIB, and IIB),

Dossmann, H.; Fontaine, L.; Weisgerber, T.; Bonnet, V.; Monflier, E.; Ponchel, A.; Przybylski, C.

Inorg. Chem. 2021, 60, 930-943.

Cyclodextrins (CDs) are cyclic oligosaccharides mainly composed of six, seven, and eight glucose units, so-called α-, β-, and γ-CDs, respectively. They own a very particular molecular structure exhibiting hydrophilic features thanks to primary and secondary rims and delimiting a hydrophobic internal cavity. The latter can encapsulate organic compounds, but the former can form supramolecular complexes by hydrogen-bonding or electrostatic interactions. CDs have been used in catalytic processes to increase mass transfer in aqueous–organic two-phase systems or to prepare catalysts. In the last case, interaction between CDs and metal salts was considered to be a key point in obtaining highly active catalysts. Up to now, no work was reported on the investigation of factors affecting the binding of metal to CD. In the study herein, we present the favorable combination of electrospray ionization coupled to mass spectrometry [ESI-MS(/MS)] and density functional theory molecular modeling [B3LYP/Def2-SV(P)] to delineate some determinants governing the coordination of first-row divalent transition metals (Mn2+, Co2+, Ni2+, Cu2+, and Fe2+) and one post-transition metal (Zn2+) with α-, β-, and γ-CDs. A large set of features concerning the metal itself (ionic radius, electron configuration, and spin state) as well as the complexes formed (the most stable conformer, relative abundance in MS, CE50 value in MS/MS, binding energy, effective coordination number, average bond lengths, binding site localization, bond dissociation energies, and natural bond orbital distribution) were screened. Taking into account all of these properties, various selectivity rankings have been delineated, portraying differential association/dissociation behaviors. Nonetheless, unique 3D topologies for each CD–metal complex were emphasized. The combination of these approaches brings a stone for building a compendium of molecular features to serve as a suitable descriptor or predictor for a better first round rationalization of catalytic activities.

A simple procedure to obtain a medium-size oligogalacturonic acids fraction from orange peel and apple pomace wastes,

Cano, M. E.; García-Martín, A.; Ladero, M.; Lesur, D.; Pilard, S.; Kovensky, J.

Food Chem. 2021, 346, 128909.

Pectin oligosaccharides, which can be obtained from fruit wastes, have proven their potential as plant immune-system elicitors. Although the precise size of active species is still under investigation, medium size oligosaccharides have been reported as the most active. Three defined oligogalacturonic acid (OGAs) mixtures were produced from commercial pectin, orange peel and apple pomace residues. The methodology developed involves two sequential acid treatments followed by stepwise ethanol precipitation. Without the need of chromatographic separations, three different fractions were obtained. The fractions were analyzed by high performance anion exchange chromatography (HPAEC) and were completely characterized by mass spectrometry, showing that the small size, medium size and large size fractions contained OGAs of degree of polymerization 3 to 9, 6 to 18, and 16 to 55, respectively.

Start-up G+Lyte - Trophée de l'innovation dans la catégorie transition énergétique

La start-up G+LYTE, soutenue par le CNRS et CNRS Innovation est lauréate du Trophée de l'innovation dans la catégorie innovation transition énergétique !
Ce prix lui a été décerné par l'agence d'innovation Hauts-de-France Innovation

Graphene quantum dots: From efficient preparation to safe renal excretion,

Hadad, C.; González-Domínguez, J. M.; Armelloni, S.; Mattinzoli, D.; Ikehata, M.; Istif, A.; Ostric, A.; Cellesi, F.; Alfieri, C. M.; Messa, P.; Ballesteros, B.; Da Ros, T.

Nano Research 2020.

Carbon nanomaterials offer excellent prospects as therapeutic agents, and among them, graphene quantum dots (GQDs) have gained considerable interest thanks to their aqueous solubility and intrinsic fluorescence, which enable their possible use in theranostic approaches, if their biocompatibility and favorable pharmacokinetic are confirmed. We prepared ultra-small GQDs using an alternative, reproducible, top-down synthesis starting from graphene oxide with a nearly 100% conversion. The materials were tested to assess their safety, demonstrating good biocompatibility and ability in passing the ultrafiltration barrier using an in vitro model. This leads to renal excretion without affecting the kidneys. Moreover, we studied the GQDs in vivo biodistribution confirming their efficient renal clearance, and we demonstrated that the internalization mechanism into podocytes is caveolae-mediated. Therefore, considering the reported characteristics, it appears possible to vehiculate compounds to kidneys by means of GQDs, overcoming problems related to lysosomal degradation.

Physicochemical, foaming and biological properties of lowly irritant anionic sugar-based surfactants,

Bois, R.; Abdellahi, B.; Mika, B.; Golonu, S.; Vigneron, P.; Chagnault, V.; Drelich, A.; Pourceau, G.; Wadouachi, A.; Vayssade, M.; Pezron, I.; Nesterenko, A.

Colloids and Surfaces A: Physicochemical and Engineering Aspects 2020, 607, 125525.

Surface-active compounds derived from biomass, especially sugar-based amphiphiles, have received wide attention regarding their biodegradability, low toxicity and ecological acceptability. Compared to nonionic sugar-based surfactants, the anionic ones show significantly better solubility, higher surface activity and foaming performance. Thus they are largely used in personal care formulations and many technological applications. However, anionic surfactants are well known to induce skin and eye irritation. In this study, three sugar-based anionic surfactants, bearing a lipidic chain grafted to the anomeric position of a monosaccharide (glucose or xylose) and a sulfate group on the primary hydroxyl, were synthesized: 6-O-sulfo-N-(β-d-glucopyranosyl) dodecanamide (GlcNC12S), N-dodecyl-6-O-sulfo-d-gluconamide (GlcCC12S) and N-dodecyl-6-O-sulfo-d-xylonamide (XylCC12S). These molecules were investigated in details for their self-assembling behavior, foaming properties and biological ef7452fects. All their properties were compared to those of two commercially available anionic surfactants, sodium laureth sulfate (SLES) and sodium dodecylsulfate (SDS). Results revealed that the three anionic glycolipids show surface properties and foaming behavior comparable to those of SDS. Furthermore, their cytotoxic and irritation potentials are significantly lower compared to commercial molecules, which make these renewable molecules potential candidates for replacement of petroleum-based compounds.

Insight on the Contribution of Plasmons to Gold-Catalyzed Solar-Driven Selective Oxidation of Glucose under Oxygen,

Golonu, S.; Pourceau, G.; Quéhon, L.; Wadouachi, A.; Sauvage, F.

Solar RRL 2020, 4, 2000084.

With the increasing concerns about pollution and reduction of energy demands, the use of solar energy to drive chemical transformations is becoming increasingly attractive. Within the context of sustainability, sunlight-driven organic transformation of biomass feedstock, such as free carbohydrates, to obtain high added-value products is an important topic in which the recent progress should contribute to the development of solar biorefineries. Among the variety of photocatalysts, gold nanoparticles (NPs) loaded onto large bandgap semiconductors represent the state of the art. Such catalysts are known to accelerate the targeted reaction upon plasmonic excitation. In addition, as noble metal NPs, they also hold an additional role related to surface catalysis, which has been exploited for aerobic oxidation of free sugars. Nevertheless, the respective contribution of each role during transformation is not well established. Herein, the enhancement of the O2-mediated oxidation of free sugars using Au NPs on CeO2 under standard air mass 1.5G illumination conditions is reported. The results highlight that the plasmonic contribution of Au NPs is totally annihilated and this enhancement stems solely from a thermal activation process induced by NIR radiation from standard white-light conditions.

First step to the improvement of the blood brain barrier passage of atazanavir encapsulated in sustainable bioorganic vesicles,

Nolay, F.; Sevin, E.; Létévé, M.; Bil, A.; Gosselet, F.; El Kirat, K.; Djedaini-Pilard, F.; Morandat, S.; Fenart, L.; Przybylski, C.; Bonnet, V.

Int. J. Pharm. 2020, 587, 119604.

The blood - brain barrier (BBB) prevents the majority of therapeutic drugs from reaching the brain following intravenous or oral administration. In this context, polymer nanoparticles are a promising alternative to bypass the BBB and carry drugs to brain cells. Amphiphilic cyclodextrins can form self-assemblies whose nanoparticles have a 100-nm-diameter range and are thus able to encapsulate drugs for controlled release. Our goal is to propose an optimized chemical synthesis of amphiphilic cyclodextrin, which remains a challenging task which commonly leads to only a low-milligram level of the high purity compound. Such cyclodextrin derivatives were used to prepare vesicles and to study their ability to vectorize a drug through the BBB. As a result, we introduced a convergent synthesis for a family of lipophosphoramidyl permethylated β-CDs (Lip-β-CDs) with various chain lengths. It was demonstrated that mixed vesicles comprised of phosphatidylcholine (POPC) and LipCDs were able to encapsulate atazanavir (ATV), a well-known protease inhibitor used as an antiretroviral drug against HIV. We highlighted that neo-vesicles promote the penetration of ATV in endothelial cells of the BBB, presumably due to the low fusogenicity of Lip-β-CDs.

Synthesis of defined oligohyaluronates-decorated liposomes and interaction with lung cancer cells,

Cano, M. E.; Lesur, D.; Bincoletto, V.; Gazzano, E.; Stella, B.; Riganti, C.; Arpicco, S.; Kovensky, J.

Carbohydr. Polym. 2020, 248, 116798.

In this work hyaluronic acid (HA) oligosaccharides with degree of polymerization (DP) 4, 6 and 8, obtained by enzymatic depolymerization of HA, were conjugated to a PEG-phospholipid moiety. The products (HA-DP4, HA-DP6 and HA-DP8) were used to prepare decorated liposomes. The cellular uptake of HA-DP4, HA-DP6 and HA-DP8-decorated fluorescently labelled liposomes was significantly higher (12 to 14-fold) in lung cancer cell lines with high CD44 expression than in those with low CD44 expression, suggesting a receptor-mediated entry of HA-conjugated formulations. Competition assays showed that the uptake followed this rank order: HA-DP8>HA-DP6>HA-DP4 liposomes. Moreover, they are capable of a faster interaction with CD44, followed by phagocytosis, than HA liposomes obtained from HA of higher molecular weight (4800 and 14800 Da). HA-DP4, HA-DP6 and HA-DP8-liposomes did not show cytotoxicity or inflammatory effects. Overall, we propose our new HA-DP oligosaccharides as biocompatible and effective tools for a potential drug delivery to CD44-positive cells.

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